US6825218B1 - Spherical agglomerates of telithromycin, their preparation process and their use in the preparation of pharmaceutical forms - Google Patents
Spherical agglomerates of telithromycin, their preparation process and their use in the preparation of pharmaceutical forms Download PDFInfo
- Publication number
- US6825218B1 US6825218B1 US10/049,874 US4987402A US6825218B1 US 6825218 B1 US6825218 B1 US 6825218B1 US 4987402 A US4987402 A US 4987402A US 6825218 B1 US6825218 B1 US 6825218B1
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- telithromycin
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- spherical agglomerates
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- crystals
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- MSSSIXOPKQWXTO-MFAXCEABSA-N CC[C@H]1OC(=O)[C@H](C)C(=O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@H]2N(CCCCN3C=NC(C4=CN=CC=C4)=C3)C(=O)O[C@]12C Chemical compound CC[C@H]1OC(=O)[C@H](C)C(=O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@H]2N(CCCCN3C=NC(C4=CN=CC=C4)=C3)C(=O)O[C@]12C MSSSIXOPKQWXTO-MFAXCEABSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1682—Processes
- A61K9/1688—Processes resulting in pure drug agglomerate optionally containing up to 5% of excipient
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Definitions
- a subject of the present invention is spherical agglomerates of telithromycin, their preparation process and their use in the preparation of pharmaceutical forms.
- the oral route is a preferred form of administration for this product.
- Telithromycin is an active ingredient which has an unpleasant taste. Galenical forms must therefore be produced which mask the taste of the product yet preserve a good bioavailability.
- telithromycin The physico-chemical properties of telithromycin are such that they permit micro-encapsulation, i.e the coating of the active ingredient with a polymer or a mixture of polymers.
- the micro-encapsulation can be carried out by spraying a polymer or by interfacial polymerization or by coacervation.
- spherical particles of active ingredient must be available, particles which are neither too small, to prevent them from agglomerating among themselves, nor too large, in order that the dissolution is not too slow, and the particles must be spherical so that the covering of the active ingredient by the polymer is correct and in order to obtain good release kinetics for the active ingredient.
- a subject of the invention is spherical agglomerates of telithromycin.
- the spherical agglomerates are obtained as shown below by direct transformation of the crystals into masses of spherical shape.
- the agglomerates of the invention permit a good micro-encapsulation and a subject of the invention is in particular the use characterized in that the spherical agglomerates are surrounded by a layer of polymer in order to obtain the sought galenical form, for example micro-capsules.
- a subject of the invention is spherical agglomerates of telithromycin characterized in that the size of the particles is between 30 and 400 microns.
- a quite particular subject of the invention is spherical agglomerates of telithromycin characterized in that the median size of the particles is situated between 80 and 150 microns and in particular spherical agglomerates of telithromycin characterized in that the median size of the particles is situated towards 100 microns, i.e. characterized in that half of the agglomerates are less than 100 microns in size.
- a subject of the invention is also a process for the preparation of spherical agglomerates characterized in that a suspension of telithromycin crystals is prepared, and these crystals are then coated with a phase insoluble in telithromycin which progressively crystallizes.
- a subject of the invention is in particular a preparation process characterized in that a solution of telithromycin in acetone is used.
- a more particular subject of the invention is a preparation process characterized in that the crystallization takes place in an acetone/isopropyl ether mixture.
- the crystallization is carried out between ⁇ 5 and ⁇ 15° C.
- the size of the spherical agglomerates is controlled by adjusting the stirring speed.
- a subject of the invention is spherical agglomerates of telithromycin as obtained by the preparation process described above.
- the temperature is stabilized between 19° C. and 21° C. 5% by mass of the acetone solution is introduced, while stirring at 350 rpm.
- Crystallization develops immediately after initiation.
- Drying is carried out in an oven at 40° C. under vacuum, followed by sieving on a 500 ⁇ m grid.
- the size of the particles is determined by laser diffraction using a HELOS SYMPATEC® model granulometer.
- the results obtained are the following: 10% of the particles have a diameter of ⁇ 77 microns 50% of the particles have a diameter of ⁇ 107 microns 90% of the particles have a diameter of ⁇ 166 microns.
- FIG. 1 represents agglomerates obtained by operating as shown above, the scale being
- the product of the example was used to prepare, by simple coacervation or by direct spraying of a suitable polymer, micro-capsules intended for the preparation of oral suspensions to be prepared extemporaneously.
- the prepared suspensions are accepted by children and retain good release kinetics.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Epidemiology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention relates to spherical telithromycin clusters and to a method for the production thereof characterized in that a telithromycin crystal suspension is prepared, said crystals are coated with a telithromycin insoluble phase which gradually crystallizes. The spherical telithromycin clusters are used in the preparation of micro-capsules.
Description
This application is a 371 of PCT/FR00/02393 filed Aug. 28, 2000.
A subject of the present invention is spherical agglomerates of telithromycin, their preparation process and their use in the preparation of pharmaceutical forms.
Telithromycin or 11,12-dideoxy-3-de((2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribohexopyranosyl)oxy)-6-O-methyl-3-oxo-12,11-(oxycarbonyl((4-(4-(3-pyridinyl)-1H-imidazol-1-yl)butyl)imino))-erythromycin is a product endowed with antibiotic properties of structure: 
described and claimed in European Patent 680967.
The oral route is a preferred form of administration for this product. Some patients, children in particular, have difficulty in swallowing tablets and capsules and therefore it is desirable to have available other forms of administration such as for example oral suspensions, ready to use or prepared extemporaneously at the time of use.
Telithromycin is an active ingredient which has an unpleasant taste. Galenical forms must therefore be produced which mask the taste of the product yet preserve a good bioavailability.
The physico-chemical properties of telithromycin are such that they permit micro-encapsulation, i.e the coating of the active ingredient with a polymer or a mixture of polymers.
The micro-encapsulation can be carried out by spraying a polymer or by interfacial polymerization or by coacervation. In order to obtain a good micro-encapsulation, spherical particles of active ingredient must be available, particles which are neither too small, to prevent them from agglomerating among themselves, nor too large, in order that the dissolution is not too slow, and the particles must be spherical so that the covering of the active ingredient by the polymer is correct and in order to obtain good release kinetics for the active ingredient.
A subject of the invention is spherical agglomerates of telithromycin.
The spherical agglomerates are obtained as shown below by direct transformation of the crystals into masses of spherical shape.
As regards spherical agglomerates in general, reference may be had to the article by Frederica Guillaume and Anne-Marie Guyot-Hermann in Il Farmaco XLVIII 1993 pages 473 et seq.
The agglomerates of the invention permit a good micro-encapsulation and a subject of the invention is in particular the use characterized in that the spherical agglomerates are surrounded by a layer of polymer in order to obtain the sought galenical form, for example micro-capsules.
A subject of the invention is spherical agglomerates of telithromycin characterized in that the size of the particles is between 30 and 400 microns.
A quite particular subject of the invention is spherical agglomerates of telithromycin characterized in that the median size of the particles is situated between 80 and 150 microns and in particular spherical agglomerates of telithromycin characterized in that the median size of the particles is situated towards 100 microns, i.e. characterized in that half of the agglomerates are less than 100 microns in size.
A subject of the invention is also a process for the preparation of spherical agglomerates characterized in that a suspension of telithromycin crystals is prepared, and these crystals are then coated with a phase insoluble in telithromycin which progressively crystallizes.
A subject of the invention is in particular a preparation process characterized in that a solution of telithromycin in acetone is used.
A more particular subject of the invention is a preparation process characterized in that the crystallization takes place in an acetone/isopropyl ether mixture.
In a preferred embodiment, the crystallization is carried out between −5 and −15° C. The size of the spherical agglomerates is controlled by adjusting the stirring speed.
Finally a subject of the invention is spherical agglomerates of telithromycin as obtained by the preparation process described above.
The following example illustrates the invention without, however, limiting it.
a) Preparation of the Acetone Solution
The following are introduced under nitrogen:
telithromycin 64 g
anhydrous pure acetone 128 ml
Stirring is carried out under a slight nitrogen overpressure between 19° C. and 21° C. and a check is carried out to ensure that the dissolution is total.
If necessary, the quantity of water is added to obtain a 2.9% product, adding:
demineralized water 0.26 ml.
b) Crystallization
The following are introduced under nitrogen, into a double-casing reactor fitted with a mechanical stirrer, a thermometric probe and a nitrogen inlet:
isopropyl ether 640 ml
anhydrous pure acetone 12.8 ml
The temperature is stabilized between 19° C. and 21° C. 5% by mass of the acetone solution is introduced, while stirring at 350 rpm.
Then, while still stirring at 350 rpm, the crystallization is initiated with 0.96 g of micronized telithromycin suspended by sonication in:
isopropyl ether 3.2 ml
Crystallization develops immediately after initiation.
Stirring is carried out for 15 minutes at 20±1° C. then the suspension is cooled down to −10±1° C. over 30 minutes.
The rest of the acetone solution is introduced:
acetone solution of telithromycin 157.2 g
Stirring is carried out for another 1 hour at −10° C.
c) Isolation
Thorough drying and washing by clarifications are carried out twice with, each time:
isopropyl ether 64 ml.
Drying is carried out in an oven at 40° C. under vacuum, followed by sieving on a 500 μm grid.
50.4 g of spherical agglomerates of telithromycin are obtained.
Granulometry
The size of the particles is determined by laser diffraction using a HELOS SYMPATEC® model granulometer.
The results obtained are the following: 10% of the particles have a diameter of <77 microns 50% of the particles have a diameter of <107 microns 90% of the particles have a diameter of <166 microns.
FIG. 1 represents agglomerates obtained by operating as shown above, the scale being
1 cm=150 microns.
The product of the example was used to prepare, by simple coacervation or by direct spraying of a suitable polymer, micro-capsules intended for the preparation of oral suspensions to be prepared extemporaneously.
The prepared suspensions are accepted by children and retain good release kinetics.
Claims (6)
1. A process for the preparation of spherical agglomerates of telithromycin crystals, comprising preparing a suspension of telithromycin crystals, and coating the crystals with a phase in which telithromycin is insoluble from which telithromycin progressively crystallizes.
2. The process of claim 1 , wherein a solution of telithromycin in acetone is used.
3. The process of claim 1 , wherein the crystallization takes place in an acetone/ispropyl ether mixture.
4. The process of claim 1 , where the crystallization is carried out between −5° C. and −15° C.
5. A method of treating a bacterial infection in a human comprising administering orally without an unpleasant taste to a human in need thereof an antibactercidally effective amount of a compound of a spherical agglomerate of telithromycin crystals surrounded by a layer of at least one polymer.
6. A method of forming a micro-encapsulated form of spherical agglomerates of telithromycin comprising surrounding spherical agglomerates of telithromycin with a layer of a polymer to obtain the micro-encapsulated form.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9910810A FR2797875B1 (en) | 1999-08-26 | 1999-08-26 | SPHERICAL TELITHROMYCIN AGGLOMERATES, PROCESS FOR THEIR PREPARATION AND THEIR APPLICATION IN THE PREPARATION OF PHARMACEUTICAL FORMS |
| FR9910810 | 1999-08-26 | ||
| PCT/FR2000/002393 WO2001014393A2 (en) | 1999-08-26 | 2000-08-28 | Spherical telithromycin clusters, method for the production and use thereof in the preparation of pharmaceutical forms |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US6825218B1 true US6825218B1 (en) | 2004-11-30 |
Family
ID=9549351
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US10/049,874 Expired - Fee Related US6825218B1 (en) | 1999-08-26 | 2000-08-28 | Spherical agglomerates of telithromycin, their preparation process and their use in the preparation of pharmaceutical forms |
Country Status (34)
| Country | Link |
|---|---|
| US (1) | US6825218B1 (en) |
| EP (1) | EP1212336B1 (en) |
| JP (1) | JP4871467B2 (en) |
| KR (1) | KR100718222B1 (en) |
| CN (1) | CN1183151C (en) |
| AR (1) | AR025398A1 (en) |
| AT (1) | ATE255590T1 (en) |
| AU (1) | AU774385B2 (en) |
| BR (1) | BR0013569B1 (en) |
| CA (1) | CA2382497C (en) |
| CO (1) | CO5190666A1 (en) |
| CZ (1) | CZ2002594A3 (en) |
| DE (1) | DE60006976T2 (en) |
| DK (1) | DK1212336T3 (en) |
| EA (1) | EA005080B1 (en) |
| ES (1) | ES2209970T3 (en) |
| FR (1) | FR2797875B1 (en) |
| HK (1) | HK1049167B (en) |
| HR (1) | HRP20020167B1 (en) |
| HU (1) | HU229075B1 (en) |
| IL (2) | IL148128A0 (en) |
| ME (2) | MEP20108A (en) |
| MX (1) | MXPA02001988A (en) |
| NO (1) | NO322622B1 (en) |
| PL (1) | PL204100B1 (en) |
| PT (1) | PT1212336E (en) |
| RS (1) | RS50433B (en) |
| SI (1) | SI1212336T1 (en) |
| SK (1) | SK287588B6 (en) |
| TR (1) | TR200200506T2 (en) |
| TW (1) | TWI272949B (en) |
| UA (1) | UA73523C2 (en) |
| WO (1) | WO2001014393A2 (en) |
| ZA (1) | ZA200201599B (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030134875A1 (en) * | 1999-06-10 | 2003-07-17 | Karol Horvath | Production of agglomerates |
| US20040091536A1 (en) * | 2001-03-09 | 2004-05-13 | Julien Meisonnier | Telithromycin suspension with masked taste |
| US20070082854A1 (en) * | 2005-10-06 | 2007-04-12 | Alembic Limited | Novel polymorphs of erythromycin compound |
| US20090075917A1 (en) * | 2007-09-19 | 2009-03-19 | Protia, Llc | Deuterium-enriched telithromycin |
| US20110020442A1 (en) * | 2002-07-19 | 2011-01-27 | Aventis Pharma S.A. | Taste Masked Oral Composition of Telithromycin |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004009059A1 (en) * | 2002-07-19 | 2004-01-29 | Aventis Pharma S.A. | Taste masked oral composition of telithromycin |
| MXPA05000322A (en) * | 2002-07-19 | 2005-03-31 | Aventis Pharma Sa | Taste masked oral composition of telithromycin. |
| WO2004073827A1 (en) * | 2003-02-21 | 2004-09-02 | The University Of Bath | Process for the production of particles |
| US20050014706A1 (en) * | 2003-07-14 | 2005-01-20 | Kanakeshwari Falzari | Method of treating tuberculosis |
| KR101324862B1 (en) * | 2011-07-12 | 2013-11-01 | (주)에이에스텍 | Spherical particle of clopidogrel bisulfate, pharmaceutical composition comprising the same and method of preparation thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0130160A2 (en) | 1983-06-22 | 1985-01-02 | The Ohio State University Research Foundation | Small particle formation |
| JPH02227130A (en) | 1989-02-28 | 1990-09-10 | Taisho Pharmaceut Co Ltd | Manufacture of spherical, frozen fine particles |
| EP0680967A1 (en) | 1994-05-03 | 1995-11-08 | Roussel-Uclaf | Erythromycin derivatives, their process of preparation and their use as medicaments |
-
1999
- 1999-08-26 FR FR9910810A patent/FR2797875B1/en not_active Expired - Fee Related
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2000
- 2000-08-02 TW TW089115526A patent/TWI272949B/en not_active IP Right Cessation
- 2000-08-18 CO CO00062195A patent/CO5190666A1/en active IP Right Grant
- 2000-08-25 AR ARP000104426A patent/AR025398A1/en unknown
- 2000-08-28 AT AT00958756T patent/ATE255590T1/en active
- 2000-08-28 UA UA2002032354A patent/UA73523C2/en unknown
- 2000-08-28 PL PL353137A patent/PL204100B1/en unknown
- 2000-08-28 IL IL14812800A patent/IL148128A0/en active IP Right Grant
- 2000-08-28 RS YUP-132/02A patent/RS50433B/en unknown
- 2000-08-28 CA CA2382497A patent/CA2382497C/en not_active Expired - Fee Related
- 2000-08-28 WO PCT/FR2000/002393 patent/WO2001014393A2/en not_active Ceased
- 2000-08-28 TR TR2002/00506T patent/TR200200506T2/en unknown
- 2000-08-28 AU AU70181/00A patent/AU774385B2/en not_active Ceased
- 2000-08-28 DE DE60006976T patent/DE60006976T2/en not_active Expired - Lifetime
- 2000-08-28 SK SK253-2002A patent/SK287588B6/en not_active IP Right Cessation
- 2000-08-28 DK DK00958756T patent/DK1212336T3/en active
- 2000-08-28 ME MEP-201/08A patent/MEP20108A/en unknown
- 2000-08-28 HK HK03101349.3A patent/HK1049167B/en not_active IP Right Cessation
- 2000-08-28 CN CNB008120943A patent/CN1183151C/en not_active Expired - Fee Related
- 2000-08-28 HR HR20020167A patent/HRP20020167B1/en not_active IP Right Cessation
- 2000-08-28 ES ES00958756T patent/ES2209970T3/en not_active Expired - Lifetime
- 2000-08-28 KR KR1020027002404A patent/KR100718222B1/en not_active Expired - Fee Related
- 2000-08-28 EP EP00958756A patent/EP1212336B1/en not_active Expired - Lifetime
- 2000-08-28 CZ CZ2002594A patent/CZ2002594A3/en unknown
- 2000-08-28 EA EA200200294A patent/EA005080B1/en not_active IP Right Cessation
- 2000-08-28 US US10/049,874 patent/US6825218B1/en not_active Expired - Fee Related
- 2000-08-28 ME MEP-2008-201A patent/ME00112B/en unknown
- 2000-08-28 PT PT00958756T patent/PT1212336E/en unknown
- 2000-08-28 JP JP2001518723A patent/JP4871467B2/en not_active Expired - Fee Related
- 2000-08-28 SI SI200030287T patent/SI1212336T1/en unknown
- 2000-08-28 MX MXPA02001988A patent/MXPA02001988A/en active IP Right Grant
- 2000-08-28 BR BRPI0013569-0A patent/BR0013569B1/en not_active IP Right Cessation
- 2000-08-28 HU HU0202842A patent/HU229075B1/en not_active IP Right Cessation
-
2002
- 2002-02-12 IL IL148128A patent/IL148128A/en not_active IP Right Cessation
- 2002-02-26 NO NO20020926A patent/NO322622B1/en not_active IP Right Cessation
- 2002-02-26 ZA ZA200201599A patent/ZA200201599B/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0130160A2 (en) | 1983-06-22 | 1985-01-02 | The Ohio State University Research Foundation | Small particle formation |
| JPH02227130A (en) | 1989-02-28 | 1990-09-10 | Taisho Pharmaceut Co Ltd | Manufacture of spherical, frozen fine particles |
| EP0680967A1 (en) | 1994-05-03 | 1995-11-08 | Roussel-Uclaf | Erythromycin derivatives, their process of preparation and their use as medicaments |
Non-Patent Citations (2)
| Title |
|---|
| Graul et al, "HMR-3647, An Antimicrobial Ketolide", Drugs Future (1998) vol. 26, No. 6, pp. 591-597, XP 000909275. |
| Guillaume et al., "Spherical Crystallization of Meprobamate", Il Farmaco, vol. 48, No. 4, 1993, pp. 473-485. |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030134875A1 (en) * | 1999-06-10 | 2003-07-17 | Karol Horvath | Production of agglomerates |
| US20040091536A1 (en) * | 2001-03-09 | 2004-05-13 | Julien Meisonnier | Telithromycin suspension with masked taste |
| US20110020442A1 (en) * | 2002-07-19 | 2011-01-27 | Aventis Pharma S.A. | Taste Masked Oral Composition of Telithromycin |
| US20070082854A1 (en) * | 2005-10-06 | 2007-04-12 | Alembic Limited | Novel polymorphs of erythromycin compound |
| US20090075917A1 (en) * | 2007-09-19 | 2009-03-19 | Protia, Llc | Deuterium-enriched telithromycin |
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Effective date: 20161130 |